Robert Greene and Ryan Holiday on Ego and Power | LIVE in LA

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1:39Welcome to the weekend edition of The Daily Stoic. Each weekday, we bring you a meditation inspired by the ancient Stoics, something to help you live up to those four Stoic virtues of courage, justice, temperance, and wisdom. And then here on the weekend, we take a deeper dive into those same topics. We interview Stoic philosophers. We explore at length how these Stoic ideas can be applied to our actual lives and the challenging issues of our time. Here on the weekend, when you have a little bit more space, when things have slowed down, be sure to take some time to think, to go for a walk, to sit with your journal, and most importantly, to prepare for what the week ahead may bring.

2:30Hey, it's Ryan. Welcome to another episode of the Daily Stoic Podcast. I'm excited. I'm going this summer to one of my favorite places on earth, a place I haven't been in a little over 10 years now, a place I haven't been since I had kids. But one of my favorite places to swim on earth, which I'm thinking about now, my ankle's still messed up, so I'm not running. So I'm just craving awesome places to swim. And I can't wait to get in those rock pools in Bondi Beach in Australia. But I'm going to be in Sydney on the 31st of July, and then I believe Melbourne on the 1st of August. You can find tickets to that at ryanholiday.net slash Australia.

3:15But I won't be bringing Robert Green with me on those dates. Unfortunately, I know he's actually the one that told me about those pools. So I know he's going to be a little jealous. But Robert and I back in September did a talk at the Wilshire Ebel Theater, talked about AI and ego, success and failure, discipline, memento mori. And it was just an absolutely awesome experience. The Ebel Theater was a theater I used to run past when I lived in that part of Los Angeles, when I was just starting out being Robert Greene's research assistant. It was awesome. And I thought I'd bring you that talk as sort of a bonus episode.

3:55I think Robert's been on the podcast more than just about any person alive. And they're always the most popular episodes that we do. So here's Robert and I on stage talking at the Wilshire Ebel Theater. And if you want to see me live in theater on the other side of the world. Come see me in Australia in July and August, and you can grab tickets. I'll link to that in today's show notes. You can grab tickets at ryanholiday.net slash Australia.

4:40Thank you all for coming. This is very cool. So what we're going to do is Robert and I are going to talk for a little bit, and then we'll open it up to questions from all of you. And we'll do this. Where should we put that? I hope they're here for security just so I don't fall. And you can tap it for emphasis. And I get really angry. I thought we should start with our mutual first love. A thing I think some people think is dry or dusty or boring, although if they thought that, they probably came to the wrong talk and are reading the wrong two authors. But there's something about history that I think lights me up, and I know it lights you up.

5:24Talk to me about why history does that and why it's so important for people to read. Okay, first off, I want to say I'm incredibly honored to see so many people here. I'm from Los Angeles. I know at least half of you are here to see Ryan, but still, I'm deeply honored. I live a very lonely life, so seeing all these people is pretty incredible. um well you know i for the last thank you thank you

5:57i mean it i mean it so for the past 28 years i can say that i've spent an incredible amount of time with dead people right i've probably interacted more with the dead than the living during that time you know all the books that i read and so i have a very particular relationship to the dead. I'm not talking about the rock group. So, you know, first of all, when you focus on what it means to be alive, I like to start there. So each one of you in the audience is alive. You have your own particular consciousness, your own sort of mindset. And it has this sort of texture to it, this day by day texture that kind of makes who you are.

6:41It's your daily thoughts. It's your obsessions it's your patterns it's your emotions etc and you it's hard to qualify you couldn't you can't feel it you can't taste it or see it but it's who you are and you live it and then when it comes to decisions in your life there's moments where you could go this direction that direction this direction and you choose a path and sometimes it's the wrong path sometimes it's a good path I can honestly say I never intended in my life to write the 48 laws of power. I didn't start out at eight years old. I'm going to write the 48 laws of power. I kind of went like this, this, this, this, this, this.

7:18And I ended up doing it, you know, by chance almost. So when we look at the past and we look at those who lived before us, they are the same as you and I right now. They have the same consciousness, the same sort of sense of time of being in the present. they were alive they had that little filter that made them who they were their individuality their emotions their big choices in life and so when I write about history and I read a lot of books of history and I can tell you 98 % of them bore the crap out of me they are so boring they are so dry they just list George Washington on November 4th he woke up he talked to his troops that afternoon he crossed the Delaware River, blah, blah, blah, blah, blah.

8:08It's like we make the dead people even more dead than they are, right? So, but they're alive. They're in the moment. They're excited. They're, you know, they're dealing with the same things that you're dealing with right now. So I often think of the example that comes to my mind when I write, because I'm trying to, when I write about a character, to make the reader feel that they're alive, just like you are right now. I think of Julius Caesar at the moment when he was about to cross the Rubicon and enter into the civil war against Pompeii, one of the most dramatic moments in history. And if you put yourself in his shoes, here's this man who's just been through the Gallic Wars, incredibly violent, you know, with the barbarians of France, the Gauls and all that he'd been through.

8:55And he's seen so many deaths, nearly died. and here he is with 50 ,000 troops and if he crosses the river, it's civil war and he's facing Pompey, who's got an army five times his size, right? And we just think he just crosses the river and he says the die is cast and such and such. But no, he's afraid, he's hesitant. He knows that if he crosses, he's probably gonna die, right? And lots of his men are going to die. it's an incredibly dramatic moment and he's hesitating and he's thinking about the options and he's thinking about where he came from where this will be at the end of his life and then he comes to that moment where he decides to cross it but that's like incredibly dramatic it's not like this just fact it wasn't like he was fated he had to cross the Rubicon it was a choice that he made and I want to give a feeling when you're reading books about history that these people are alive, that they're living through moments just like you and to make history something so much more exciting and dramatic and romantic in a way.

10:06Yeah, the great biographer, David McCulley, he said something that I really love. He said, you can never lose sight of the fact of two things. One, that they didn't live in the past. They lived in the present. And two, it could have gone differently, right? And so what we're talking about in our books, what he's talking about in his books, what you're talking about there with Julius Caesar is that he didn't have to do it. It was only a foregone conclusion after it happened. And so when you can see history as this sort of snapshot of something as it's happening, as opposed to something that did happen, it becomes exciting, really exciting.

10:47Yes, there's the fact that there's been the spoiler that you vaguely know what happened because you heard about it in school or, you know, all this artist based on. But if you can go back and you're reading it and you go, they were really wrestling with something. There was something hanging in the balance here. And, you know, the great man of history theory is obviously less in vogue today than it was in the past. But to go like, if this person had chosen differently, if something had gone a little bit differently, all the events that came after would have gone differently. And so suddenly the stakes become very high and you really feel the humanness of that moment as opposed to just a bunch of dry sentences in a book.

11:29There's a whole series of books out called What If? And they're fascinating. I don't know if you ever read them. And so they go through history. If one little detail had turned differently, all of history would have been rewritten and probably I don't know where we would be. So one of the best examples is the Mongols under Genghis Khan, their invasion of Europe. And they were on the verge of going to Vienna and conquering Vienna. And then all of Europe would open up. And then I think it was Genghis Khan died. And they all had to return for his funeral because that was their religion. And so they never did it.

12:05But if he died a week later and they had launched their invasion of Vienna, all of European history would have been completely altered. And these are amazing things to consider. And it's the sort of macro enormous events like this. And then on a much smaller level, like with what I write about, I think something that struck me as I'm reading meditations is Marcus Aurelius thinks his philosophy teacher, Rusticus, who gives him his copy of Epictetus's lectures. And so if that doesn't happen, if the teacher doesn't recommend a book to the student, and then the student doesn't read the book, the book that I'm reading in this moment doesn't exist.

12:46And then the whole notion of the philosopher King Marcus realizes life goes perhaps differently. And so how just as our lives individually can be changed by the single intervention of a person or an idea or a book at the right time, at the right place, that's also happening historically with these people that you're reading about. A single, you know, Theodore Roosevelt's father doesn't say, hey, you're smart, but you're weak, and you've got to get strong. These singular moments change the course of someone's life, and thus history that follows. I'll take it one step further. If you hadn't come and contacted me some 16 years ago, right, you wouldn't have been writing about the Stoics and had your books, and people wouldn't be reading about Marcus Aurelius from you right now.

13:35None of these people would be here, and in fact, they might not even exist.

13:42I love what you said about living or interacting with the dead, because that's also a very stoic idea. Do you know about the prophecy that Zeno gets from the Oracle at Delphi? Refresh me. He's a young man and he's a merchant, so he's traveling all around. And he stops at the Delphi and he goes to the Oracle and he gets his prophecy. And they tell him, you will become wise when you begin to have conversations with the dead. And the whole point of the oracle is that you never know what they're talking about. And it's vague. And the meaning reveals itself to you later. And it's not until he suffers the shipwreck.

14:17He washes up in Athens. He has nothing. And he sort of stumbles into a bookstore. They had bookstores? Yeah. Well, where do they get these books? I mean, they're not, you know, your and my books. But this is where you're buying the scrolls or the writing materials. Well, I didn't know that. Yeah, of course. so I mean we don't know the name right is it an indie bookstore is it a chain bookstore you know but he ends up in this he ends up in this bookstore and the bookseller is reading one of Plato's dialogues or I know I guess it would have been one of Xenophon's books he's reading Socrates on the choice of Hercules and it's in this moment that Zeno realizes what the prophecy means that you'll become wise when you begin to have conversations with the dead that's what reading is that's what history is that's what books are it's the way that these people come alive it was as if socrates was in that bookstore with him right it was as if hercules was in that bookstore with him because that's what the power of even bad history is but great history vividly written history it's a chance to revive these hundreds of thousands millions of incredibly wise men and women who live before us.

15:33They have all these amazing things to teach us about how to live in the present, right? All these lessons for us. And to ignore that is just unbelievably stupid, right? And so, you know, history is a compendium of all of the most incredible human mistakes ever made. It's a compendium of human stupidity. And the dumbest people and the smartest people are all in books. Yeah. So there's so much to learn from that. And to ignore that incredible wealth that's sitting before you is, to me, kind of tragic. What's worse than tragic if you're in a position of leadership, if you're a parent, if you have anyone that is dependent on you in any way, because you're going to be learning by trial and error or by painful experience.

16:23and they're going to have to pay that bill with you, right? So the idea that you're in uncharted territory or you're on breaking new ground, you're not at all. People have been in this exact place as you or an analogous place as you. Not only have they been there, but someone's been there and they did it well and someone's been there and didn't do enough. Someone's been there and fucked it up. And how would you not avail yourself of that information? The idea of sort of starting where they left off is so vastly superior than going, well, I want to start from scratch. There's one other aspect to history, though.

17:05There's one kind of caveat there. If you watch a lot of movies nowadays that are kind of historical dramas, you look at them, people are acting just like people nowadays. They talk like they talk nowadays. they're swearing etc they look like anybody that you would see on hollywood boulevard on friday afternoon right sure but it's totally bogus it's a complete myth you know there's a book called the past is a foreign country right and it's true the people in the past there's they have the same emotions as us but their cultural differences are vast they don't think the same way so the other great thing about history is, for instance, I was obsessed, obviously, with Machiavelli and the Italian Renaissance, but also with the French court of Louis XIV.

17:53And I really got into how, what it was like to be in the court at Versailles. And the way of thinking and the formality and the rituals is not at all how we think nowadays. And so we're so locked into our cultural moment with our phones and our politics and everything now, that we don't realize that there are other ways to think. There are other perspectives on life. And history can open up a completely alien way of looking at problems, et cetera, if you're culturally sensitive, if you spend the time researching.

18:30I got an amazing night's sleep last night. One, because my six-year-old fell asleep in the car at like six o 'clock and he transferred him from the car seat to the bed and it stuck, which is just magic. So he's in bed way earlier than normal. But I sleep really well every night because I have a Eight Sleep Pod 5 Ultra, which is Eight Sleep's best product. I've used Eight Sleep for many years now and it's just totally transformed how I sleep, made me sleep better, made my wife sleep better. It's amazing. So basically, Eight Sleep is this topper that goes over your mattress. It can heat and cool both sides separately.

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21:32Well, there's a narcissism. You think everyone's like you, everyone thinks the same way as you. The same way we do this to animals, like you're projecting onto your dog that your dog's... But in fact, your dog has... There's a German word, is it umwelt? You know, the experience that they're having is different. It's defined by their species. It's defined by their limitations. It's defined by the moment of time you're in. And so, yeah, there's something really trippy in the past where you can see yourself in it and you go back and you feel connected to it. And then there's other parts that are so inexplicable and impossible to fully understand.

22:10And I think you have to have both in your head at the same time. So true. Do you know what? I'm going to give you another German word now. Ungeheimlich. It's the uncanny. that's the definition of the uncanny something that's both familiar and strange at the same time like in a dream yeah something that seems like i kind of know that person but i don't know them and that's what history is like yeah it's very true i i like even that it's a foreign country because people are people right so you travel to another country and they're still you they still do most of the same things they do but then they have these cultural assumptions that are so different or ways of being and and you just go oh that's that's very different and then it forces you to think about why you do the things that you do some of the things you go that's a bad way of doing it in other words why do we do it the way that we do it well um i'm for my new i'm writing a book on the sublime right now and i have a chapter on pagan religions and i got very deeply into greek religion and the gods and their notion of religion and gods is so alien to us but it's so beautiful and it's actually something that you can think about in the present and apply to your life their idea is gods are not these living entities out there in the sky you know like we see in movies they're these kind of vibrating presence in nature that you feel kind of pass through you an energy that passes through you so that when Aphrodite passes through you it creates this kind of weird sexual energy in you but when Demeter passes through you it creates a whole different feeling or another god or zeus or whatever there's a presence in the world that passes through you and takes hold of you and possesses you but this idea of being possessed by nature by other forces outside of us is actually to me very relevant in the future i don't believe in zeus i don't worship zeus right but there is something actually there that when you think about it there is some truth to what they how they were describing the universe yeah that is really interesting sorry no no no it makes sense and and i think yeah sometimes we go oh they can't really have believed these things because we are sort of projecting our modern cynicism backwards but they did oh very much so very much so yeah i i describe in the book the um the eleusinian mysteries and the actual route they take to go to eleusis and the whole process and i take you through it and it's like this incredible drug experience and they actually did have hallucinogenic drugs at the end right but the sense of being possessed by this god is very real they believe it and they they take you on this journey where you actually think that you die because they put you in this situation where you feel like you've died and everything is dark around you etc and then you're reborn it's very dramatic and very powerful and very real this is a slight aside but i was telling my oldest the story of odysseus and um i had this weird experience i'm telling him you know the story of the cyclops and you know the cyclops asks odysseus what his name is and he says my name is no man and uh you know so i can watch him sort of note that and then i'm telling the whole story and then you get to the punch line of you know who did this to me and he says no man or who did this to you he says no man and and it's and he just starts cracking up like he gets the joke he's laughing very very hard and and it's was his moment.

25:36It's like, here's this, what, three, four, several thousand year old joke that's slamming as if I just came up with it right then. And the timelessness of that. And so so many parts of the Odyssey are inexplicable, you know, as he gets there, not to spoil the ending, but, you know, he just, there's just this sort of moment at the end where he just, you know, murders with his bare hands, like a hundred people. And it's just like, of course he did right you know doesn't he kill the scooters bow and arrow well he and his son tell me because they slaughter them you know it's a very brutal ending which i had to skip over but the point is i mean to your son yes yes the point is some parts why would you skip over that well he's a little young that kind of stuff six felt a little young to have a hundred people be murdered um not for me i tell you not for me this may have been why you ended up writing the 48 laws of power someone told you some dark stories when you're a six um very true so some parts of it beyond comprehension and then other parts work perfectly and that's i think encapsulates you know what it means to be yeah so talking about the distant past of course but then you know they were in the present moment i think one of the things i took during covid i it struck me um as someone who loves history, you know, you have these sort of, you know, I have all these moments that are happening right after each other.

27:00And I just had this thought, I was like, oh, this is what living through history feels like, you know, because it wasn't fun to go through these, the things that I like to read about that get me excited. I of course know what happened and I'm only largely hearing about the people who survived. But you're like, it's not necessarily fun to live through history. That's the Chinese expression about may you live in interesting times. What do you think of the present moment we're in now what's your what you talk a lot about the zeitgeist and laws of human nature what do you think about where we are now well you know um each each period tends to have a kind of feel to it right like the 20s it was kind of the wildness after world war one people are going crazy alcohol sex the whole thing the 30s the depression and reacting to that and the 40s and the war and the war years the 50s and eisenhower and we all know the 60s you know okay and uh and you know i personally i'm old enough i can actually say i lived through the 60s and the 70s right in the 70s were kind of like this great hangover from the 60s and then but i think about now and my whole thing is what's it going to be how are people a hundred years from now going to be writing about this present moment that we're in and the strange thing is, is I can't really get a handle on it.

28:23I really feel like we live in this time that is so weird and chaotic that it's really hard to put a name on it. It's really hard to figure out what is actually going on. And I think a hundred years from now, maybe they will understand it, but it's so strange. So we don't have like large belief systems anymore. Like there was the war, There was communism versus the West. There was capitalism, the fall of the Berlin Wall and all these tremendous, traumatic moments we lived through, you know, 9-11, et cetera. But what is kind of defining this? What unifies us? So in the 20s or the 60s, you had like the wildness going on, the sex, the alcohol, the drugs.

29:11And you had the reaction against it. People were very conservative. But it was kind of this one whole fabric. I can't find anything like that right now. I think a lot of it comes from technology and the Internet, where we're all so splintered, that there's really hard to tell a story about what we're living through right now. And that's kind of how I define it. I've never really come upon a moment in history that I can say about that. And I think we're actually hungering for something kind of larger and transcend some sort of larger narrative that we can piece together about our present moment.

29:46But we don't have it right now. One thing that hit me not too long ago, it sort of made me throw up in my mouth a little bit. But it was realizing that I was born in the late 80s. So the 90s are sort of the first decade I really remember. And realizing that the 60s are as far from the 90s as we are from the 90s. I do that all the time. And you go, oh, wow. Okay. So the distance gets clear there, but then also sort of shrinks. And as I think about this moment, I think you're right. There's not sort of a shared consensus anymore. Chuck Klosterman wrote a great book called The 90s. And he was sort of talking about how, you know, September 10th, there were newspapers all over the country.

30:30And they were all doing their own headlines about what's happening in that city. Right. And then September 10, 2001, that every market was its own market. And one of the things that happens after 9-11 and then with the advent of the Internet is that everything is now national or global. And so it's interesting that we don't feel like we're a part of some big thing, but actually everything is more aligned than it is less fractured. Because there's less regional things. Even politics, they used to say all politics is local, but politics is actually local politics now is infected with national and global issues in a weird way.

31:14So I think there is this kind of thing where we're all in the same boat hearing and watching and talking about largely the same things because everything is instantaneous with the internet. And then I would maybe define the zeitgeist also by an absence of anything working particularly well. Like what institution, what organization, what group, like who or what would anyone describe as functioning particularly well? Like who's doing great? Do you know what I'm saying? Like what institutions are thriving? What organizations are thriving? It seems like most things are in some form of disarray or disillusion.

32:00Why do you think that is? I don't know. Oh, wise man. I don't know. I mean, do you have an idea? Technology is obviously a disruptive force. a lack of um you know i think one of the reasons that a lot of the institutions aren't working is that they didn't do their jobs in big moments of stress so there's like they talk about young people like uh you know millennials and then gen z and then it's like they don't believe in capitalism or democracy or something because their entire life it has not been functioning well So there's this kind of disillusionment that comes from never, they don't buy any of the logic or the stories or the narratives because they've only seen it prove to not be true.

32:51But then why aren't they kind of creating their own world, their own mist, their own narrative, a new way of looking at the world? That's what we need from this young generation. It's a disgusting world they've inherited from the boomers, et cetera. And I can speak that, you know, I am one of them. so you guys really let us down completely see you as gen x though i don't know why i feel like you're more of a gen x i'm on the borderline of it you know it depends on how i feel during the day whether i want to yeah but um you know if i were young i'd be really angry i'd be wanting something else i'd be creating something new i'd be creating new styles i would be now i don't necessarily blame them because it's you know looking at that you know it's easy to say that you know i didn't grow up in the internet generation i didn't have that kind of effect on my thinking but you know when there should be something there should be a real sense of malaise and anger it's a critical moment we have to create something new we have to create a new world order here instead we're just we're creating i know we're going to get on to this just doing toys technological toys ai etc we need a cultural movement now something coming up from the bottom that's going to rescue us in this moment you're not an ai fan right no we were talking about that earlier why not well you know how some foods can kind of rot out your body how they're not good for you they taste good but they're not really good for you right i think of ai in that way okay so um you know i i uh i study a lot of languages that was sort of my major in college and i'm thinking back to the moment when i was 19 years old and i was at berkeley and i decided on the whim of sudden whim i was going to take this six-week course where you learned one year of ancient greek in six weeks it was like the craziest thing i've ever been through right Every day you had an exam.

34:58Every Friday you had a final exam. You were thinking you were dreaming in ancient Greek. It was a fantastic experience, right? And I remember at one point near the end, they gave us a passage of Thucydides, Thucydides, the hardest writer of all to read in ancient Greek. It's just impossible to decipher. I can go into the nuts and bolts. It's not even easy in English. it's not even easy in English no it isn't you know you could read a sentence like 20 different ways so I had this one paragraph and I must have spent like 10 hours trying to translate one paragraph I couldn't figure it out I thought and I thought and I thought finally I go hmm I think this is the answer I think this is and I was kind of excited and I thought this is how it's going to work and I turned it into my professor this kind of crazy hippie classics professor and he goes Robert I see what you were thinking I see where you were going you were almost there but you missed it you completely mistranslated this beautiful paragraph but you were getting at something and that had an incredible impact on me even to this day it made me realize that whenever you face a problem that you don't quite understand you have to think you have to think more deeply you have to use that anxiety of is this right no it's not totally right I have to go deeper into it deeper and deeper and deeper and i use that as a model for all of my work now when i'm writing a chapter or something you haven't figured this out you have to go you have to think more about it right you don't have it right well what if in that moment i'd simply pulled out my translation of thucydides and just copied the paragraph yeah but what if i had chat gpt and i just put it in there and it gave it to me right away my thinking the whole thinking process would have been annihilated right there the whole process of the the frustration oh i can't get it oh i'm not good enough something's wrong with me oh i gotta go further and further and further it developed character it developed patience it developed discipline it developed self-esteem and humility there's nothing more humiliating than facing a paragraph for 10 hours and not figuring it out right sure so you've got you know kids nowadays who are never going to have that that experience sure they're going to be you know getting prompts they're going to be no one's going to learn a foreign language anymore because you can just go to go to mongolia and type in a sentence in chat gbt will give you the translation sure these incredible skills that the brain has are going to be atrophying, I really fear, I fear.

37:41And that kind of process, the brain is so much more interesting to me than any piece of technology, I'm sorry. That's what we should be worshipping, not these little toys that we create. Someone was asking me...

38:01Someone was asking me actually just the other day about the sort of notecard research system that I learned from you. And they were sort of, they were like, can you walk me through some of the pros and cons of doing sort of by hand note cards? And I said, well, the thing about the note card system is that all of the cons are actually pros, right? The fact that it is hard, that you can't scale it, that it takes forever, that your hand aches, that if you want to put one note card in two places, you have to do it two times. You know, that it's physical, that you can lose. All of that is actually why it works.

38:42Because you read something in a book, and then if you want to get it from the book to the note card to maybe put it in your book or use it in a speech or whatever, you have to physically take it from here. It has to flow from your mind through. It's this process, right? And that it's hard is the reason that it works and that you could highlight it and pass it from here to there and make an infinite number of all the things that digital technology allows you to do are advantages in the sense that they remove the difficulty. But by removing the difficulty, they remove the point. They remove all the value.

39:19Yeah. The writer Douglas Hofstetter said, if you want to climb Mount Everest, right, you have to spend weeks training and training and training and training. And then you finally reach the moment where you get there and it's really horrible and the oxygen and everything. And you could die and you've got your Sherpas who might be dying. You finally get to the top. Whoa, how incredible. He said, Chad GPT is the equivalent of taking a helicopter to the top of Mount Everest and getting the same view. Or just somebody showing you a picture of it. At least you got to see the view as a person. You're getting a refraction of a refraction of a refraction with these things, I think.

40:03Right. Yeah. You know, you were the best researcher I've ever had by far. Thank you. Right. So it was amazing. Okay. I had the worst researcher a couple years ago. I hope he's not here. I imagine whoever it is doesn't think that they're the worst one, right? Oh, no. God, no, no. And you know what he did? I told him my note card system. What he did is he literally digitally copied passages from the books. And I don't know how he did it. He, like, printed them on the note cards. He didn't take the time to write and to think about what they might be. He just copied passages on note cards. I could just read the whole book instead of going through your stupid note cards sometimes I type the passages I don't feel like it's cheating it's still flowing through I'm doing it because because my handwriting I can't get it all on the card it's the only way I can shrink the font down I don't print it on the card to punish myself I print it out And then I cut it out with scissors and then I tape it or I get one of my kids glue sticks.

41:22I put that on. Wouldn't it save so much more time just doing it by hand? Well, for two reasons, no. One, again, the handwriting is so, I can't get it in there. And then oftentimes that can introduce, my handwriting is so bad I've found that I've been introducing errors. And then I have to go back to the text. So I'll get it right the first time. All right, all right, all right. I forgive you. It's all right. It's not a sin. That's okay. Yes. But no, the fact, do you ever read a book that's so good and you're excited as you're reading it, but then also you're dreading that what it's going to take out of you at the end when you have to go through your note cards to do it in the note, I go, oh my God, this is, I'm looking at the book and it's like every page is folded.

42:09I go, I'm basically going to have to rewrite this book by hand. I know. I have that all the time. Yeah. Yeah. More often I have a book that sucks so badly that it's not even worth half a note card. Yes. Yes. Sometimes they're worth like 60 note cards. And you're like, oh, shit, I got to spend like four days, you know, copying that out. I know. You had a three by five or a four by six? I'm a four by six guy. I'm a four by six guy. You know what I started doing? We're nerding out. You know what I started doing? This is how I knew I made it. Didn't I tell you to do four by six? Yeah, of course. Of course.

42:41I get my own note cards printed for each book. What do you mean? Like with the title of the book at the top of the note card. I don't understand. Are you OCD or something? No, no, what I'm saying is you can get your regular people note cards at the store, but these are four by six note cards. These are fancy. These are like monogrammed note cards. It says the title of the book at the top of the note card. so i'll give you okay so for the for the virtue series i'm doing the the four virtue series right courage discipline justice okay so it this is what i did for this but actually it was a little different than what i'm saying so i got like 10 000 note cards printed uh from a printer down the street from the bookstore and it says courage uh discipline justice wisdom at the top of the note card and when i'm doing the note cards i circle which book that note card is going to pertain to because you're researching more than one book at a time well sometimes i'm fine i'm reading a book there's such good stuff but it's it's not for the book i'm doing now i want i'm use it later and then okay so i've actually i've taken your system not for a singular book i've had to i have four boxes for four books yeah okay and so some of the stuff that i didn't use in the first book moves over to the second which moves over to the third so i'm playing you know four dimensional you're you're you're much better organized than i am because first of all you take only like a year or two to write a book i take like five years or so and you know i i know that there's something in there that will be good for my next book but by the time i get to my next book so many years have passed like it's just useless for me you know i want to talk i want to talk about that.

44:26So first off, the reason my books are faster than yours is they're about a tenth of the length. So we're running totally different rates. It's like a sprinter being faster than someone running a marathon or an ultra marathon in your case. I mean, talk to me about how do you work on something every day for five years? Like, how do you how do you delay gratification also how do you how do you keep yourself going when i mean let's say for the first year you're not even 20 of the way done right like i'm just trying to wrap like you don't even feel like the progress of getting closer to the end really how do you keep going well in the beginning you're all excited you're like an eager puppy about to go for a walk you know you've got all of this material the whole world is open i can read all of these books it's fun then it starts getting a little bit painful after about a year but the saving grace is each chapter is different each chapter is like a book right sure so i'm writing a book now on what i call the sublime the first chapter is about the history of the universe so I'm reading all of these science books I've read this chapter it's like millions of years of history and billions yeah it's it's incredible okay yeah and you know like I read a book called the first three minutes which is about the first three minutes of the universe it's an incredible book very technical but incredible you know the big bang right and then I'm immersed in that and then it's over after about five months and now i'm writing a book about evolution and the dinosaurs i'm going into the world of dinosaurs and animals and biology wow how exciting and then that's over by the end i'm kind of drained and then i'm moving on to pagan religions each chapter is so exciting and different and weird and human nature was like that you know rationality narcissism how can you not be excited about writing a chapter about narcissism there's so much material i had so much material from myself as well you know it's fun but if i had to write one book on narcissism for five years i would kill myself i would never make it so the diversity of it and the breadth of it is the feature because it allows you to get excited about the component parts but i can tell you when you're like in chapter five and you've got seven more to go and you go, oh man, I don't know if I can make it.

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49:23Like when I swim, if I'm swimming a mile, which is a long distance, I get tired. I don't swim a mile. I swim like seven sets of 10. Yeah, I do the same thing. And then I go, and then I got to do a couple more at the end, right? Like, and so, so what I'm feeling is not, I'm feeling like if I do one lap, oh, I'm 10 % of the way done with a set. And then two, okay, now I'm, and so I'm breaking it down to these pieces that I'm creating the sense of momentum, the sense of being over the hump for this smaller component part. And so I'm never, you're not actually ever dealing with this sort of period of Paul Graham, when you talked about in mastery, you know, he says there's the launch and then he says, you immediately go into the trough of despair.

50:08Yeah. But I feel like if you break things up into component parts, you're actually never in the trough of despair because you're always just starting a set or you're just finishing a short set. So breaking it up is a really good way to do hard things that take a long time. That leads me to a question I wanted to ask you. So, you know, your books have helped me a lot. I read them all the time. My favorite is Ego is the Enemy, but they're all really great. But I like struggle with these things all of the time. So I meditate every morning and as I'm going through my meditation, thoughts are piling up, going outside of me and going, I'm like, man, that's my ego talking.

50:49My ego is talking. I'm heading towards enlightenment in my meditation. I'm going, wow, if I get enlightened, I'll be so much better than anybody else. I will be the enlightened one. And all these other suckers, they're not. My ego, my ego is constantly bubbling up. Discipline, I'm always like, man, I'm so bored. I'm just going to read more about the Lakers. and I'm going to get into some trivia kind of thing. I'm struggling constantly with these things. You, the great master genius of these things, do you struggle as well, particularly with ego, which you described so brilliantly in the introduction to ego is the enemy?

51:31Are you still dealing with that? Well, not only did writing the book not solve the problem for me, I then had to get it tattooed on my arms as a constant daily reminder.

51:45I'm better than most people at it. I would say I wrote about it because it's a thing I'm struggling with constantly. Especially, I think what was unique for me, particularly with ego, your story is, you're the sort of classic late bloomer. I mean, you wrote 40 Laws of Power. How old were you? I have to say, I was 38 years old, like older than you are right now. Yeah. which is so different than my experience and there's pros and cons to both but I think

52:21my first book came out I sold my first book when I was 24 years old and then it got an option to be a television show all this stuff happened so young I think about what I saw when I was going through at American Apparel none of that was healthy or normal

52:43and I think it would have been very easy to spin off the plan. So clearly this stuff worked at some level, but also the formative influences in my 20s were not people who lasted. I mean, they imploded and blew up their lives and burned out. And so I'm definitely having to think about that stuff all the time. Like who are you talking about? Well, Dove's a good example. He's not doing so great. But I mean, the idea is like these people that I thought were teaching me how to do stuff were in fact teaching me a longer lesson on how not to do stuff. Oh, you don't include me in that. No, no. You're the last one standing.

53:29Yeah, well, you know, success is a very dangerous thing. Yeah, you say success is more dangerous than failure. For sure. Or damaging than failure. Particularly when you're young. And it's the kind of classic scenario that happens to hip-hop artists. One-hit wonders, you know. They're 22, 23. They have a great hit. They've got all the fame suddenly. They had nothing before that. And it's like a drug and it goes to their head. And they can't do anything after that. It paralyzes them. And then afterwards, if their second album bombs, which usually happens, it's a phenomenon. they don't have the internal fortitude the discipline the skills the character to deal with it so success early on is very very dangerous and i can say for me i had nothing but failure until i was 38 you know my parents were starting to get really worried about their son right i had 50 different jobs i had never worked more than 11 months at one job right okay so i knew failure man i knew what it's like to work in the worst boring offices with all the worst politicking going on so i could never take it for granted i could never rest on my laurels and go wow i'm successful it's not drug you know i i knew how hard it was to get there and i knew each time i write a book it could fail you know even at this point i still think my books are going to fail so having it's terrible to wait till you're 38 it's better to do it when you're 24 but it's also a blessing in a way i'm more fati it is what it is so you i think i got lucky in the sense that you know i did a book when i my first book came out when i was 25 and it hit a bestseller for a week and then you know i had to take a big step back when i sold the obstacles away i had to take half what I've gotten from my first book.

55:24Is that right? Yeah, the publisher basically was sort of like, well, I guess, you know, and they, I remember someone told me they thought it would sell 5 ,000 copies of The Obstacles Away. And that it would sell? That was their guess. And what is it now? About 2 million. Whoa!

55:45But, you know, actually they looked like they would be more right than wrong at first. I mean, it sold, it did okay. the first week, but it didn't hit any best service. And then it kind of just dribbled along. You know, it didn't really start taking off until it had been out for a year. And it sold more each subsequent year, but there was no one moment where it just hit, right? And so it was quick, but then really steady. And so there was an adjustment curve to it. And I was too busy doing the next book and the next book and the next book to really notice how quickly it was picking up. And so, you know, I think if you're one of the ways, I think the antidote against the poison that is potentially success, like Tennessee Williams calls it the catastrophe of success, right?

56:38If you get it all at once, it can wreck you. If you're just working, if you're working on the next thing or the next problem, you are too busy to celebrate. You're too busy to let it go to your head. You're too busy to say that it says something about you as a person. You're just on to the next thing. That's a great lesson. I mean, I think of like, let's take Dove, for example, you know, a classic example. And - This is Dove Charney, the founder of American Apparel. Yeah. And so he's an incredible entrepreneur. He's very charismatic. You know that we both kind of fell under his spell initially.

57:19And he becomes incredibly successful. An amazing story. This guy selling T-shirts out of his car in Montreal to this factory in Los Angeles. This beautiful factory employing thousands of people in Los Angeles doing regular work, being paid well. Hundreds of millions of dollars a year in sales. Amazing story. but he can't hold on to it. Why? That success, he can't adapt. So it's the classic story of someone who's really good at one thing, and he's really good at building the company and creating the design and the marketing, but he can't adjust to the next level, which is, I'm running a large company.

58:05I'm not a good manager of people. I'm kind of crazy. I'm insane, right? I yell at people. I'm out of control. I've got to get other people to handle it for me. But he can't make that adjustment. So your success is often makes you a prisoner of things that worked for you in the past. I've often used Dove as an example. I've told people, you know, on its face, the idea is insane. I'm going to make clothes in America. I'm going to pay people fairly. I'm going to not put logos or branding on them. I'm going to run my own stores. I'm going to do the photographs myself. It's going to, everything that he did made it less likely that it would work potentially.

58:49It's all crazy, right? So everyone told him every step of the way, this is a bad idea. It won't work. Don't do it. And so the catastrophe of his success is that he proved all those people wrong. Now he can't do anything wrong. Yeah. And he identifies that voice of don't do that. It's a bad idea with those same very wrong people. And it becomes almost synonymous with haters or non-believers. And when they would say, hey, I think you should hire a better accounting staff or you should bring in these people to support you or, hey, it's not only a bad idea ethically and morally, but it's illegal to have sexual relations with the people who work for you.

59:32And he's like, what do you know? You know, and he's so the C the success is the seed of his own destruction. And in some ways it's almost inevitable. Well, look, he was a huge fan of the 48 laws of power. He called it his Bible. He called me El Señor, which is deeply blasphemous. Okay. Right. And so he has me on as a consultant. He brings me on to the board of directors. Right? And you would think that he would trust my advice, that he was going to listen to me. El Señor is giving him advice. But every time I tried to tell him, no, you can't do that, Dove. You need to change. What worked in 2003 with young women wearing this kind of sexy 80s clothes isn't where they're at in 2011.

1:00:26Things are changing. You have to adapt. You have to think about what the next step is in what the trends are. Oh, yeah, yeah, yeah, yeah, yeah. He never listened to anything I said. And yet, so that to me is like, you know, and I deal with that all the time as a consultant. People hire me to give them the advice that they wanted to hear in the first place. Right. So, yeah, I remember there was one, the only person at some point who could reach him. I remember it got so bad that somebody called his mom and his mom came and sort of pulled him out of a spiral. He was that when he was sleeping in the factory.

1:01:02Yes. There's some Elon Musk vibes. Oh, my God. It's totally Elon Musk. It's eerie how similar it is. It's the same kind of personality trait, the certain disorder, the same micromanaging, the same thinking like I can do no wrong. Even the stupidest little tweet I sent out is brilliant. you know? Yeah. It's, it's, it's really weird. And I think one of the things I took from that is a sort of a wariness of kind of like very manic energy, bad habits, lack of structure. Like, uh, I, obviously I wrote ego is the enemy as American apparel was pulling itself to pieces. But then the book I did after was about stillness was me trying to rebuild my life after out of the destruction, the way I'm going.

1:01:49I remember I was, I like, I don't know, I called someone that worked for me at like two in the morning. And my wife was like, what are you doing? You know, you can't call people. This isn't how this works. But that's the habit that I had picked up and I had watched. You know, I remember Dove would sometimes call me like late at night because he had to hear talking before he could go to sleep. He was one, so lonely, but two, so dysregulated that like he had to sort of, that's how he would come down. And it was realizing like, oh, that's not where good decisions come from. The sort of manic energy to come up and then the things to come down.

1:02:32You've told the story, but maybe you could at that famous board meeting where the decision to what happened. Jesus, I hope he's not here today. I'm sure he came to visit. He and Kanye are both here. That would be interesting. Are they friends? No, he's running Kanye's fashion company. Oh, my God. What a pair. What a pair. The anti-Semite and the Jewish hustler. God, yeah. So, you know, it's a very dramatic moment. Wait, sorry, I did talk to someone at American Fair. I said, we were both there and we've been through all those epic, like, five. I was like, how do you think their meetings go? When they sit down, who talks for five hours without break?

1:03:13Is it Kanye that gets to do it? Is it Dove that gets to do it? You know, they must just be fighting each other to be the craziest one. I don't know. I don't know. Maybe we have to join their company again and find out. Then they call Elon and they just go. Yeah, yeah. There's a movie in there. Sorry. So, yes. No, no, no. The famous scene. Yeah, well, like, so just put yourself in this position. I'm his friend. he we literally we'd hang out we'd hang out in new york hang out here we'd go to bars we'd go to restaurants we were friends because the guy's really interesting he's funny he's weird he's manic but he's also very interesting and he's a genius he's a genius but there's a point reached where this this ship is going down right and it's going down fast and he's crazy and he's running it into the ground.

1:04:03And we've got 12 ,000 employees to look after. We have shareholders. It's a publicly traded company. We have responsibility to the shareholders on the board of directors. So we decide that we have to fire him, right? And I'm the linchpin of this, I hate to say, because as supposedly put on the board to be loyal, if I say no, then there's no way we can fire him but i kind of go along yes we have to fire this guy it's it's terrible and so we have to disguise the whole it's a conspiracy like you wrote about right with peter teal yes we can't tell anyone because the moment he hears anything of this we're dead meat he's going to fire every one of us and replace us right so it's like something you know like a cia and we have to We keep everything secret, all our emails, all our correspondence.

1:04:56And then we go to New York for the board meeting where we're going to fire him. And, you know, quite nervous. You know, what's this going to be like? And Dov comes into the room for a meeting and he doesn't know what to expect. And the guy was, I don't know if you've ever seen the movie The Cain Mutiny. With, okay, it's before your time. It's Henry Bogart. Plays this captain of a ship who's literally going insane. He's like worrying about the strawberries that are being eaten in the refrigerator on his battleship as opposed to like the battles going on. And Dove was sitting here with like Nescafe, a bottle of Nescafe.

1:05:33And he was literally eating the Nescafe scoop after scoop after scoop. Of dry coffee powder? Yes. I would have rather him just done cocaine in front of me. That's less weird. Well, he was like putting like a little bit of water in and then eating it and then scooping it out. It was really disgusting. And then we fire him and he's so shocked, right? Well, didn't you, I think what's, just for people who were getting a little into the weeds, but there was actually a choice. Isn't he offered a series of choices, sort of a rational choice? the choices were you know uh are you going to be fired with cause or without cause and in one way you you you get wasn't the third sorry wasn't the third option you can resign and get like a million dollars a year as a consultant like there was an option a rational option where you walk away the winner yeah yeah yeah yeah well he turned that down right away his his decision was to fight us every step of the way.

1:06:36And then, you know, it's all history. He goes with this billion-dollar hedge fund that he somehow manages to seduce, but they're completely using him. And then the company just totally falls apart. It's destroyed. I regret, in the end, firing him because... Just because it didn't work? Because it would have been better to have him run the ship aground and for him to realize that he failed as opposed to being able to blame us for that. Right. Yeah, the problem is ultimately people don't want to learn the lessons. No. Not from their experiences. Yeah. But I feel like you and I learned a couple lessons from it.

1:07:16Oh, yeah. Yeah. I learned. You got some good books out of it, too. You did. I learned that I can be a fool, that I can be conned, that I have a weakness, that somebody, the person who wrote about Connors and the 48 Laws of Power himself was conned, was seduced by this guy. And I was brought on as basically a patsy, a tool that would be loyal to him, that he could kind of manipulate the way he wanted to. It was a deep reckoning with my own weaknesses, to be honest with you. But you were in good company. That's something that I took from it in the sense that I watched multiple billionaires. I watched Dove give them tours of the factory.

1:07:56You know, they knew what they were getting into. They knew the history, right? They knew what had happened. They knew the lawsuits. They knew all of it. And each time he would manage to convince and persuade the so-called smartest, best judges of talent in the world to give him millions of dollars. And I watched the ability that we have to fool ourselves. You know, in Wall Street, you go, it's different this time, but also the idea, oh, it's going to be different with me right yeah yeah it's gonna work out for the mavericks with kairi irving of course it's not you know um it's character is fate the stoics would say right like that that you it's not going to be different it's it's it's it's in it's in the blood you know and and to realize how how good we are at fooling ourselves at seeing what we want to see that's one of the laws of human nature yeah it is but i you know i wrote the books about that so it's a little more galling for me to fall for it than billionaires who are going to make a lot of money out of it.

1:09:01Whereas I'm not going in for money. So, anyway. Well, I want to get to the questions, but I did think we should wrap up with the idea of mortality, the ephemerality of life. It's a good way to end. As we come to the end of the talk, I've been fiddling with this Memento Mori ring. It's sort of one of the reminders that I have this sort of physical touch. I think it's so interesting. Like in the ancient world, death was everywhere, right? Nobody died in a clean hospital down the street, you know? Nobody, very few people lived all the way to, you know, old age. Infant mortality was high. The average lifespan was shorter.

1:09:46People died in plagues and in accidents of small cuts. And then anytime you were eating animals, you saw the blood in front of you You were cutting that chicken's head right out in front of you. You saw the blood oozing out. Yeah, even warfare. It's not you're shooting an artillery shell six miles away. You're stabbing people. Yeah, and you're ripping the sword out of them. I mean, it was a gruesome world. And yet, it was the ancient world that needed, for some reason, to have these reminders of memento mori. That life is short. That you could go at any moment. That you're not invincible. the the irony is we're the ones that need the reminders because we have the evidence that you are going to live longer we have the actuary tables we have when somebody the slightest sign of sickness they're taken away and uh you know they're you're just not seeing it and so i just think it's so interesting that the people who need it most have the are the most out of touch with the fundamental fact of their existence?

1:10:51Yeah, I mean, you know, I've been thinking about it a lot lately because, as you know, I came very close to dying myself. I had a near-death experience. So I've been thinking about it a lot lately and trying to recreate what actually happened and what I could learn from it. And I decided that it's not so much death that's that's so interesting to look at it's dying itself the process of dying um and now everybody who dies obviously if they don't die suddenly they go through several weeks and they they have to go through that and there are people like myself who come back from the dead literally right and so what does it mean to actually feel like you're dying are we are we going over time I'm dying right now.

1:11:42You're good. All right. Okay. And so, you know, I think about that moment. So I was driving here in Los Angeles. Ana was in the car seat next to me. And she sees something really odd going on. And she's forcing me to pull over. No, everything's fine. Everything's fine. And then suddenly, like, I'm getting out of the car. And I'm doing all sorts of strange things. And my whole sense of time and space is shifting. It's distorting. Like, I don't know where I am. And what seems to be like 15 minutes of me doing things is actually like two minutes, which he tells me. And so then the next thing I know is I'm unconscious, right?

1:12:30And I could have easily been dead at that point. And if I'm dead, obviously I'm not here. And, you know, it's not a bad way to die. You just go to sleep and that's it. You know, it's not painful at all. Having a stroke isn't painful, generally speaking. You just, your blood stops flowing to your brain and you go, you're going conscious, right? And then I wake up and I'm in a gurney with other gurneys piled on top of me. I'm like, what the hell just happened to me? Am I actually dead right now? I don't know. I don't know. I don't know what's going on. and for a moment i'm kind of looking at myself from up above the sky and i'm looking down at my grave and my mother and honor are there kind of talking about me and i have this sense well i died that's all right life goes on etc not for you huh doesn't go on for you no it doesn't go on for me it goes on for them yeah but what wakes me up is i have to pee with incredible And then I'm alive, all right?

1:13:35I haven't died. And for some reason, I start yelling in Spanish. Yelling, suéltame, suéltame, por favor. No puedo respirar. Tengo que orinar, et cetera, et cetera. I don't know why. I'm like, my brain has been, you know, a bit jumbled up, so to speak, all right? And then the next few days, I'm like joking with everybody. And people don't understand. I'm like euphoric, right? And then, of course, a week later, I realized, no, I'm a cripple. It's the worst thing that happened to me. But I was like giddy for that first week. And when I think about it, you know, it teaches me something very elemental.

1:14:18So our idea of who we are, of the place we live in, our whole reality, it depends on our brains. Our brains construct this world for us that we take completely for granted. and we don't realize that it's actually a construction. And when your brain goes haywire like it did for me because I have a blood clot and blood isn't flowing to it, it's all an illusion. The self is an illusion. You don't actually have an ego. You don't have a self. Space and time don't really exist. They're this kind of weird, distorted mirror that we live through, but they don't actually exist. And then the most amazing thing of all is I'm alive and I carry that with me now and I go it is so strange to be alive do you understand how strange it is to be alive you have to understand that by first being nearly dead but just to be conscious just to be aware just to realize that I'm here talking to Ryan Holiday with, you know, I don't know, 900 ,000 people here is absolutely insane.

1:15:30History is insane. Automobiles are insane. Birds and cats are insane. The sheer probability of any of this existing is incomprehensible. Yeah, and it just made me so aware of that every single moment of my life. And I have a chapter in my new book, Awaken to the Strangeness of Being Alive. And so we should listen to these people who have these amazing stories coming back. I'm cataloging them and be writing about them in my new book. But dying teaches us so much about how our life is actually an illusion. It's a construction and that there's something else out there. Don't you sometimes wear the shirt as a reminder, the shirt that the paramedics do?

1:16:13So when the paramedics came, I was wearing this new shirt that Ana had got me for my birthday. and I loved it. It was this plaid shirt and I wore it all the time. They came and they like ripped it off and they cut it and shredded it in scissors, right? To get to your heart or... Yeah, to be able to get rid of the blood clot. And like eight months later, I asked Anna, where's that shirt? I love that shirt. And she told me the pathetic story of my favorite shirt. And she said, well, they actually gave it to me in a bag when you left the hospital. I go, where's that bag? She brought it to me and she pulled it out and it was in these pieces and I go, could you please sew that back together again?

1:16:53I want to wear that shirt. Speaking of memento mori, and I wear it now all the time and it's got these Frankenstein stitches across it. But hell, it looks very fashionable. And I wear that shirt with pride. And it's a reminder to you, what's so interesting is you have this powerful, overwhelming experience, but with time, I imagine it fades a little and you have to have things that bring you back to it, that connect you to the urgency of that experience? It fades, but it doesn't really fade. So I constantly dream about it. I had a feeling in my bones like life was sucking its way out of me and all the blood was leaving me and my bones were getting soft.

1:17:39I still have that feeling. I still have a visceral connection to death. And yes, it's faded, but you try spending five minutes tying your shoes every morning and you're reminded of that experience very graphically every moment of your life well it's beautiful it's haunting beautiful also

1:18:10thanks so much for listening if you could rate this podcast and leave a review on itunes that would mean so much to us and it would really help the show. We appreciate it. I'll see you next episode.

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